EP1452531B1 - Riechstoffskomponent mit Blütencharakter - Google Patents

Riechstoffskomponent mit Blütencharakter Download PDF

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Publication number
EP1452531B1
EP1452531B1 EP04100608A EP04100608A EP1452531B1 EP 1452531 B1 EP1452531 B1 EP 1452531B1 EP 04100608 A EP04100608 A EP 04100608A EP 04100608 A EP04100608 A EP 04100608A EP 1452531 B1 EP1452531 B1 EP 1452531B1
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EP
European Patent Office
Prior art keywords
compound
perfuming
formula
perfumery
cyclohexyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP04100608A
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English (en)
French (fr)
Other versions
EP1452531A1 (de
Inventor
Alvin Scott Williams
Charles Fehr
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Firmenich SA
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Firmenich SA
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Publication date
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Publication of EP1452531A1 publication Critical patent/EP1452531A1/de
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Publication of EP1452531B1 publication Critical patent/EP1452531B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals

Definitions

  • the present invention relates to the perfume industry. It concerns more particularly a compound of formula wherein R represents a linear, branched or cyclic C 1-3 hydrocarbon group, and the wavy line indicates that the substituents on the epoxide moiety may have a cis or trans configuration.
  • the compounds of formula (I), or a mixture thereof, may advantageously be used as perfuming ingredients.
  • the invention also concerns the compositions or the articles comprising as active ingredient at least a compound of formula (I).
  • analogues reported in the literature, in terms of chemical structure, are the compounds disclosed in WO 00/14051.
  • said analogues not only have a different chemical structure, i.e. a ketone group instead of an epoxide moiety, but possess also organoleptic properties which are different from the ones of the compounds according to the present invention.
  • a compound of formula (I) wherein R is an ethyl group has proved to be a remarkably useful perfuming ingredient.
  • (1S,1'R)-1-(3',3'-dimethyl-1'-cyclohexyl)ethyl trans-3,4-epoxyhexanoate is much appreciated by perfumers for its fruity odor.
  • said odor has a pronounced fruity character associated with a musky and slightly animal connotation or aspect.
  • the fruity character which is of the pear and prune type with a berry bottom note, has a remarkable persistence and is still clearly perceivable in the bottom notes. Such persistence is quite rare for this kind of ester-fruity note.
  • the overall fragrance of this compound is remarkably more fruity and powdery, and consequently much less musky, than the known analogues cited above.
  • the invention's compounds provide therefore a very interesting new tool to the perfumer's palette.
  • (1S,1'R)-1-(3',3'-dimethyl-1'-cyclohexyl)ethyl cis-3,4-epoxyhexanoate possesses a more fruity and even less musky odor than the one of the trans isomer cited above. Moreover the odor of the cis isomer is slightly less pronounced than the one of the trans isomer, making the latter a preferred embodiment of the invention.
  • Another example of invention's compound is the (1S,1'R)-1-(3',3'-dimethyl-1'-cyclohexyl)ethyl trans-3,4-epoxypentanoate which displays fruity odor notes, of the red fruit type, and a musky character as for the trans-3,4-epoxyhexanoate cited above.
  • the overall odor of said trans-3,4-epoxypentanoate is weaker than the one of the trans-3,4-epoxyhexanoate derivative.
  • Another object of the present invention is a perfuming composition
  • a perfuming composition comprising
  • perfumery carrier we mean here a material which is practically neutral from a perfumery point of view, i.e. that does not significantly alter the organoleptic properties of perfuming ingredients.
  • Said carrier may be a liquid or a solid.
  • liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery.
  • a solvent and a surfactant system i.e. a solvent and a surfactant system
  • a solvent commonly used in perfumery A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive.
  • solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, which are the most commonly used.
  • solid carrier one may cite, as non-limiting examples, absorbing gums or polymers, or yet an encapsulating materials.
  • the encapsulation is a well known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation techniques.
  • perfumery base we mean here a composition comprising at least one perfuming co-ingredient.
  • Said perfuming co-ingredient is not of the formula (I).
  • ''perfuming co-ingredient it is meant here a compound, which is used in perfuming preparation or composition to impart an hedonic effect.
  • a co-ingredient to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
  • perfuming co-ingredients present in the base do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect.
  • these perfuming co-ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S.
  • compositions which comprise both a perfumery carrier and a perfumery base can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company).
  • Isopar® oil/ethanol mixtures
  • glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company).
  • perfumery adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability and etceteras.
  • additional added benefit such as a color, a particular light resistance, chemical stability and etceteras.
  • An invention's composition consisting of at least one compound of formula (I) and at least one perfumery carrier represents a particular embodiment of the invention as well as a perfuming composition comprising at least one compound of formula (I), at least one perfumery carrier, at least one perfumery base, and optionally at least one perfumery adjuvant.
  • the invention compound can also be advantageously used in all the fields of modem perfumery to positively impart or modify the odor of a consumer product into which said compound (I) is added. Consequently, a perfumed article comprising:
  • a perfumed article according to the invention comprises the functional formulation, as well as optionally additional benefit agents, corresponding to a desired consumer product, e.g. a detergent or an air freshener, and an olfactive effective amount of at least one invention's compound.
  • suitable consumer products include solid or liquid detergents and fabric softeners as well as all the other articles common in perfumery, namely perfumes, colognes or after-shave lotions, perfumed soaps, shower or bath salts, mousses, oils or gels, hygiene products or hair care products such as shampoos, body-care products, deodorants or antiperspirants, air fresheners and also cosmetic preparations.
  • perfumes there are intended applications such as detergent compositions or cleaning products for washing up or for cleaning various surfaces, e.g. intended for textile, dish or hard-surface treatment, whether they are intended for domestic or industrial use.
  • Other perfumed articles are fabric refreshers, ironing waters, papers, wipes or bleaches.
  • consumer product bases may represent an aggressive medium for the invention compound, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation.
  • concentrations from 1% to 20%, and preferably from 5% to 15%, by weight of this compound, with respect to the perfuming composition in which they are incorporated can be typically used. Lower concentrations than these can be used when the invention's compound is directly applied for perfuming some of the consumer products mentioned above.
  • the invention concerns the use of a compound of formula (I) as perfuming ingredients.
  • a method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article which method comprise adding to said composition or article an effective amount of at least a compound of formula (I).
  • use of a compound of formula (I) it has to be understood here also the use of an invention's composition.
  • a perfume base composition of the "musky” type was prepared by admixing the following ingredients : Ingredient Parts by weight Ambrette synth. 1 Exaltolide® Total 22 Helvetolide® 25 0.1 % Perhydro-4 ⁇ ,8a ⁇ -dimethyl-4a-naphthatenol 2 Total 50 The addition of 50 parts by weight of (1S,1'R)-1-(3',3'-dimethyl-1'-cyclohexyl)ethyl trans-3,4-epoxyhexanoate to the above-described perfume base provided to the latter a pronounced fruity-waxy, pear-prune character, which was quite persistent.
  • a perfuming composition of the "floral-fruity-violet" type was prepared by admixing the following ingredients : Ingredient Parts by weight Aldehyde C10 5 Aldehyde C12 10 2-Methyl-undecenal 20 Methyl anthranilate 5 4-Phenyl-2-butanone 20 Cetalox® 10 Citronellol 50 4-Cyclohexyl-2-methyl-2-butanol 2) 100 Alpha Damascone 5 Dihydromyrcenol 100 Geraniol 20 Iso E Super® 80 Lilial® 50 10%* Neobutenone® 10 Trans-1-(2,2,6-trimethyl-1-cyclohexyl)-3-hexanol 10 Rose oxide 5 Verdyl propionate 60 10% Romascone® 10 Hexyl salicylate 150 Verdox® 120 Violettine MIP 2) 10 Total 850
  • a woman's perfume of the "fruity-musky” type was prepared by admixing the following ingredients : Ingredient Parts by weight Geranyl acetate 10 Styrallyl acetate 5 Hexylcinnamic aldehyde 40 10%* Star anise essential oil 10 Benzophenone 5 Bergamot essential oil 170 10% Ethyl (E)-2,4-dimethyl-2-pentenoate 25 Raspberry ketone 10 Citral 10 4-Cyclohexyl-2-methyl-2-butanol 1) 30 Coumarine 10 2-Pentyl-1-cyclopentol 10 2-Methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-l-ol 1) 50 Florol® 20 English Clove essential oil 5 Hedione® HC 50 10%* 3-(1,3-Benzodioxol-5-yl)-2-methylpropanal 30 Heliotropine 5 10%* Hivernal® 10 10%* Indol 10 Iralia® 10

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Epoxy Compounds (AREA)
  • Beans For Foods Or Fodder (AREA)
  • Seeds, Soups, And Other Foods (AREA)

Claims (7)

  1. Verbindung der Formel
    Figure 00160001
    worin R eine geradkettige, verzweigte oder cyclische C1-3-Kohlenwasserstoffgruppe darstellt und die Wellenlinie anzeigt, dass die Substituenten an der Epoxidgruppe eine cis- oder trans-Konfiguration aufweisen können.
  2. Verbindung nach Anspruch 1, dadurch gekennzeichnet, dass R eine Ethylgruppe ist.
  3. Verbindung nach Anspruch 2, nämlich (1S, 1'R)-1-(3',3'-Dimethyl-1'-cyclohexyl)ethyl-trans-3,4-epoxyhexanoat oder (1S, 1'R)-1-(3',3'-Dimethyl-1'-cyclohexyl)ethyl-cis-3,4-epoxyhexanoat.
  4. Duftstoffzusammensetzung, umfassend:
    i) wenigstens eine Verbindung der Formel (I) gemäß irgendeinem der Ansprüche 1 bis 3;
    ii) wenigstens einen Bestandteil, der ausgewählt ist aus der Gruppe bestehend aus einem Parfümträgerstoff und einer Parfümbasis; und
    iii) gegebenenfalls wenigstens einen Parfümzusatzstoff.
  5. Parfümierter Artikel, umfassend als Riechstoff wenigstens eine Verbindung der Formel (I) gemäß irgendeinem der Ansprüche 1 bis 3 oder eine Duftstoffzusammensetzung gemäß Anspruch 4.
  6. Parfümierter Artikel nach Anspruch 5 in Form eines festen oder flüssigen Reinigungsmittels, eines Gewebeweichspülers, eines Parfüms, eines Eau de Cologne oder einer After-Shave-Lotion, einer parfümierten Seife, eines Dusch- oder Badesalzes, einer Mousse, eines Öls oder Gels, eines Hygieneprodukts oder Haarpflegeprodukts, eines Shampoos, eines Körperpflegeprodukts, eines Deodorants oder Antitranspirans, eines Raumlufterfrischers, eines Kosmetikpräparats, eines Textilerfrischers, eines Bügelwassers, von Papieren, Wischtüchern oder Bleichmitteln.
  7. Verwendung einer Verbindung gemäß irgendeinem der Ansprüche 1 bis 3 oder einer Duftstoffzusammensetzung gemäß Anspruch 4 als Riechstoff.
EP04100608A 2003-02-24 2004-02-16 Riechstoffskomponent mit Blütencharakter Expired - Lifetime EP1452531B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IB0300650 2003-02-24
WOPCT/IB03/00650 2003-02-24

Publications (2)

Publication Number Publication Date
EP1452531A1 EP1452531A1 (de) 2004-09-01
EP1452531B1 true EP1452531B1 (de) 2005-12-28

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Country Status (8)

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US (1) US7189688B2 (de)
EP (1) EP1452531B1 (de)
JP (1) JP4280655B2 (de)
CN (1) CN1328268C (de)
AT (1) ATE314356T1 (de)
DE (1) DE602004000271T2 (de)
ES (1) ES2256820T3 (de)
IL (1) IL160516A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006039290A1 (de) * 2006-08-22 2008-03-13 Airbus Deutschland Gmbh Rahmenelement, Flugzeugkomponentenmontagesystem sowie Verfahren zur Montage einer Komponente in einem Flugzeug
WO2013045301A1 (en) * 2011-09-30 2013-04-04 Firmenich Sa Floral perfuming compositions as substitutes for lilial®

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE732205A (de) * 1968-05-09 1969-10-28
US5767305A (en) * 1997-04-03 1998-06-16 International Flavors & Fragrances Inc. Cyclopropyl carboxylic acid esters and uses thereof in imparting, augmenting and enhancing aromas
CA2309449C (en) * 1998-09-09 2005-08-16 Firmenich Sa Esters with musky odor and their use in perfumery
US6051548A (en) * 1998-11-05 2000-04-18 International Flavors & Fragrances Inc. Trimethylcyclohexenylcyclopropyl ketones perfume composition
DE60224639T2 (de) * 2001-12-05 2009-01-22 Firmenich S.A. Ungesättigter Ester als Riechstoffkomponente

Also Published As

Publication number Publication date
DE602004000271D1 (de) 2006-02-02
IL160516A (en) 2010-02-17
ES2256820T3 (es) 2006-07-16
CN1328268C (zh) 2007-07-25
US20040167059A1 (en) 2004-08-26
IL160516A0 (en) 2004-07-25
JP4280655B2 (ja) 2009-06-17
US7189688B2 (en) 2007-03-13
ATE314356T1 (de) 2006-01-15
JP2004256534A (ja) 2004-09-16
EP1452531A1 (de) 2004-09-01
DE602004000271T2 (de) 2006-08-31
CN1524855A (zh) 2004-09-01

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